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Ultimate 4-Day Chicago Experience

Ultimate 4-Day Chicago Experience Itinerary

Last updated: 2024 Jun 14

Iconic Landmarks and Skyline Views

Morning
Start your day with a delightful breakfast at Lou Malnati's Pizzeria, savoring their famous deep-dish pizza. Afterward, head to the Millennium Park to see the iconic Cloud Gate sculpture, also known as "The Bean."
Afternoon
For lunch, enjoy a classic Chicago hot dog at Portillo's Hot Dogs. Then, take a relaxing walk along the Chicago Riverwalk and admire the city's architecture.
Evening
In the evening, have a sophisticated dinner at The Signature Room at the 95th, offering stunning views of the city skyline from the John Hancock Center's 95th floor.
Bedtime
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Chicago Riverwalk

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Cultural Immersion and Culinary Delights

Morning
Enjoy a leisurely brunch at Lula Cafe, known for its farm-to-table cuisine. Afterward, visit the Art Institute of Chicago to explore one of the oldest and largest art museums in the country.
Afternoon
For a late lunch, indulge in Spanish tapas at Cafe Ba-Ba-Reeba!. Afterward, take a stroll down the Magnificent Mile for some upscale shopping and people-watching.
Evening
Have a memorable dining experience at Alinea, a three-Michelin-star restaurant known for its innovative and avant-garde cuisine.
Bedtime
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Art Institute of Chicago

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Magnificent Mile

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Museum Campus and Lakefront Serenity

Morning
Start your day with a hearty breakfast at Wildberry Pancakes and Cafe, known for its delicious pancakes. Then, visit the Field Museum to explore natural history and anthropology.
Afternoon
For lunch, enjoy some authentic Chicago barbecue at Smoque BBQ. Afterward, continue to the Shedd Aquarium to discover a diverse range of marine life.
Evening
In the evening, take a relaxing walk in Millennium Park and enjoy the serene atmosphere before having dinner at The Publican, a popular spot for its beer selection and pork-centric menu.
Bedtime
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Field Museum

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Shedd Aquarium

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Final Day of Exploration and Farewell to Chicago

Morning
For your last morning in Chicago, have a classic breakfast at The Bongo Room in Wicker Park. Then, visit the 360 Chicago Observation Deck for panoramic views of the city and Lake Michigan.
Afternoon
Enjoy a late lunch at Giordano's, famous for its stuffed deep-dish pizza. Afterward, take a guided architectural boat tour on the Chicago River to learn about the city's famous buildings.
Evening
Conclude your Chicago journey with a dinner at Girl & the Goat, a top-rated restaurant offering a creative menu with bold flavors. After dinner, take a leisurely walk along the Chicago Riverwalk to soak in the city's vibrant nightlife.
Bedtime
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Visit 360 Chicago Observation Deck (Formerly John Hancock Observatory) in Chicago
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360 Chicago Observation Deck

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Chicago River

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